2nd Date with Kristy (M/F)

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BearPlants
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2nd Date with Kristy (M/F)

Post by BearPlants »

Hi all – long time lurker, first time writer. I’m a guy in my mid-thirties with some stories to share! I’ve lived in several different parts of America over the last 15 years and am excited to write down and share my dating adventures – the ones that involve bondage at least – with this community. In all of my stories I’ll change the name for privacy’s sake, just in case! Here’s my first story about a former partner named Kristy. This happened when I was living with several roommates in an apartment in Brooklyn. There is adult content in here, so if you’re not into that – feel free to pass.

I was in my mid-twenties and was on a second date with a girl named Kristy, who was two years older than me. We’d met through a big dating website and had our first date a few days earlier. It was June, which is typically a fantastic month for outdoors activities in New York. Warm, but not yet the muggy summer of July and August.

Kristy was 5’4”, thin but athletic with pale skin, brown eyes, and semi curly light brown hair that came down a little bit past her shoulders. Socially, she would wear it down but for athletics, in a ponytail, a single long braid, or pigtail braids. She had lightly freckled skin that would come out much more so with time in the sun. I’m 6’0” and athletic. Now I have a few more pounds on me, but then I was very fit. I have blue eyes and typically rock the mostly bald/beard look with dark facial hair.

Our first date was a standard NYC date: drinks and apps at a bar that culminated in us making out for a little bit on the street before heading our separate ways home. Our second date, as we were both into cycling, was to ride down to Coney Island in Brooklyn together to spend some time at the beach and on the boardwalk. It was a lovely day, and on the way back she came back to my apartment for a snack before riding back to her apartment – which was a few more miles away.

My roommates were home so we took some veggies and hummus into my room and snacked, chatted, and flirted. We were both still in our cycling outfits: me in black spandex shorts with a white cycling jersey with red trim and black quarter length socks and Kristy in a similar outfit: black spandex shorts, a white cycling jersey with thick red stripes and white, low-cut ankle socks.

After a little while, we slowly got more comfortable in the twin XL bed I was using at the time. Still chatting about everything new couples chat about, we each slid down so that we were leaning on an elbow facing each other. She mentioned her legs being sore from the day’s ride so I slowly started massaging her quads and hamstrings, and reaching down lower to her calfs. She was very fit and the ride hadn’t been that long, so I knew the soreness was an excuse to allow me to start touching her.

She started doing the same, and soon I let my hand wander to massaging her quad and groin. I looked up at her when I made this change and got the slight smile of approval as she continued to tell me about some of her other cycling adventures. I was honestly only half listening as I got hard while I continued to rub her inner thigh and upper leg. She inched closer as we continued to converse, which was the green light to keep going as we were now only a few inches apart.

Her legs had been fairly closed since she was leaning on her elbow on her side. I slowly started to move my hand higher and closer to her crotch and she opened her legs slightly to give me more room. I heard her stop and swallow and take a deep breath before continuing to talk. I started moving my hand over her crotch more, up and down, a little bit harder. I could tell that she was having a hard time concentrating on her thoughts as she was started to breath heavier. It didn’t take much longer for her to slide onto her back and the conversation then ceased. I continued to rub her outside of her shorts and leaned in to kiss her. It was only a few seconds of us kissing and me rubbing her before she grabbed my hand and jammed it down her shorts. She looked up and smiled and breathed deeply and lowly moaned as I pushed by hand lower and lower and found her wet pussy. I slowly massaged her with my fingers before curling my index and middle fingers into her pussy and finding her g-spot. She was SO wet; they slid so easily. She was starting to moan a little bit louder as we continued to kiss. I stopped to whisper to her, “Shh, be quiet. You don’t want them to hear outside.” She again smiled and gave me a quick shake of the head. I went back to kissing and fingering her and she lay there in pleasure. She tried to stay quiet but once when I’d taken my mouth away she exclaimed “Oh!” on a particularly pleasureful stroke.

“I’m going to have to gag you to keep you quiet” I whispered, my own cock throbbing with excitement.

“Really, would you?” She asked with a smile of excitement. “Would you tie me up, too?”

“I would,” I replied. “Do you want me to?”

“I haven’t done that before,” she whispered back, obviously intrigued.

“Do you want me to?” I asked again.

She nodded her head a few times in quick succession. What luck! I got up and adjusted myself so as to not appear too obvious. She readjusted herself on my bed to get more comfortable, unsure of what to expect.

I went to my closet and took out a royal blue and black checkered cashmere scarf. I opened the bedside table drawer and took out a sleeping mask that I never use, but it’s a good excuse for a blindfold. I had Kristy slide down lower on the bed and lift her head up. I put the mask on her and let her adjust it for comfort.

“Ready?” I asked.

“Yeah,” she said from behind the mask as she smiled.

I pulled her hands up over her head and wrapped the scarf around the twice before wrapping it between her hands once to cinch it. I then wrapped each end around the top of the bed frame and tied them together to secure her to the bed. If you’ve ever used a thicker scarf, you know that you don’t have much length to play with.

I got up from the bed and walked to the end of the room and opened by dresser. I let my fingers caress down her whole leg and foot as I did this. I took out a black low cut Adidas sock and a longer black Adidas soccer sock and walked back up toward her, again letting by finger lightly drag along her body, starting from her toes up her lower leg, knee, and moving to her inner thigh. I could see her chest moving slowly up and down and watched her lick her lips. I straddled her, sitting on her stomach but keeping most of my weight on my knees. I leaned over close to her face and connected lips. I gave her a long, deep kiss before pulling away quickly and shoving the sock into her mouth. She groaned in surprise a little bit but did not resist. I pulled her head forward and pressed the sock deeper into her mouth with the soccer sock as I stretched it behind her head, and knotted it.

I unzipped her cycling jersey to reveal a navy blue sports bra underneath. I honestly didn’t notice until then but Kristy had very small breasts. This didn’t bother me however, she was incredibly sexy. I stroked by fingers down her stomach and she squirmed a little bit underneath me and laughed into her gag.

“How is this, are you okay?” I asked.

She nodded her head in approval.

“Can you snap your fingers?”

She again nodded.

“Do it for me.”

She snapped twice.

“Good. If anything is wrong or you want me to stop, just snap your fingers and I’ll stop and we can talk.”

One more time, she nodded her head.

I began by kissing her neck and rubbing her breasts. She was salty from the sweat of the ride and her nipples were rock hard from excitement. I rubbed and pinched them softly, while kissing her neck and moving to her ears. I gave her ear a little nibble and then moved by hand back down her shorts to her pussy: still wet – even more so now. I could feel how soaked through her sports underwear was. I continued to finger her and kissed her stomach. She started to moan into her gag, being louder than she was before knowing that it was muffled.

My cock was so hard it was starting to hurt inside my shorts.

I pulled her sports bra up and started to lick, kiss, and nibble on her nipples while continuing to finger her. It didn’t take long for her to really start moving around on the bed and I alternated between rubbing her clit and going deeper for her g-spot. She pulled hard against the scarf and moaning loudly into her gag as she continued to be wilder in her movements. I so badly wanted to fuck Kristy but didn’t want to disrupt anything to have that conversation. Instead, I pulled her shorts and underwear down and pushed her knees apart. I waited a few seconds for any snapping, just in case, but it never came. I quickly went down on her to bring her to orgasm. It only took a few seconds when I started using my tongue. She was close, and that put her over the edge. I could feel her body tense up and listened with pleasure to her moaning strongly into her gag while I continued to slowly massage her clit with my tongue.

A few seconds after her body relaxed, I hear faint snapping.

I quickly brought myself to her level, wiped her wetness off my face with my jersey, and began to untie soccer sock that was wrapped around her head. “Are you okay?” I asked quietly but with concern in my voice.

I removed the soccer sock and ankle sock. She didn’t answer right away. She took a few seconds to stretch her mouth and regain some saliva.

“Yes,” She finally said. “But untie me now,” she commanded, still breathing heavy.

“Okay…are you sure you’re okay? I thought you would have wanted me to…” I said.

She didn’t say anything while I untied her wrists from the bed. I backed away from her but stayed on the bed, bracing for an angry, embarrassed, or concerned march out of the room. But instead…

She tore her hands away from me and finished removing the scarf herself. She ripped the mask off her eyes and after a moment of adjusting to the light in the room, gave me an extremely devilish smile.

“My turn…” She said, almost in a whisper.

She then took me by the shoulders and shoved me on the by back, where she had just been laying. I only had a moment to be thankful that she had enjoyed herself and wasn’t about to leave.

Kristy treated me well and finished with a great BJ. We laid in bed for another 10 minutes before she sat up and I knew that it was time to end the evening. We put ourselves together before going out into the apartment, where my roommates had long departed. She used the bathroom before I walked her down to the street, where she unlocked her bike from the rack, hopped up, and rode off toward home.

Funny, how after all of that, it was a quick little look back and smile as I watched her ride away that convinced me that I would really see Kristy again (Dating in New York, after all…). We ended up dating for over a year, during which we had more bondage evenings. As I said before, I’ll be sure to write again here, soon!
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Flyingvulture
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Post by Flyingvulture »

Amazing story!
Thank you for sharing.

That moment when she said "would you?" OMG I bet that rocked your world.

I don't know how anyone could be prepared for that question.
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rtbw
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Post by rtbw »

Wow...what an evening, especially with the tie-up being unexpected. And you two were wearing very appropriate attire. This a well recounted story!
FabianStr2016
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Post by FabianStr2016 »

What a great story, and yes, I would absolutely love to hear some other stories of you two!
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Post by Mr Underheel »

More. That’s all I can say. More. Please. Great stuff! Thanks for sharing!
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Nexus
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Post by Nexus »

Great story! Would love to hear more of your experiences!
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BearPlants
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Post by BearPlants »

Thanks y'all. Appreciate the comments! Always happy to hear feedback on writing or story telling if anyone wants to PM me. I'll be sure to post another story soon!
dogrednuht123
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Post by dogrednuht123 »

[mention]BearPlants[/mention]

Great story. Absolutely loved it. Would love to hear more if you can share. Thanks.
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BearPlants
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Post by BearPlants »

dogrednuht123 wrote: 1 year ago @BearPlants

Great story. Absolutely loved it. Would love to hear more if you can share. Thanks.
Thanks [mention]dogrednuht123[/mention] ; I'm throwing up another one here soon...
Koirtza
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Post by Koirtza »

Extrem hot story!
Rtj65
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Post by Rtj65 »

Great story, really enjoyed how you described everything, Kristy sounds fun!
Male switch from the UK here, always up for a chat about anything TUGs related!

My stories
Causality (F/M) - https://tugstories.com/viewtopic.php?f=17&t=9909
A Grey Area (M/F) - https://tugstories.com/viewtopic.php?f=17&t=12604
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TheEngineer
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Post by TheEngineer »

Lovely story!
No harm in wanting to try new things right?
Always down to chat ;)
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BearPlants
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Post by BearPlants »

Thanks [mention]TheEngineer[/mention] [mention]Koirtza[/mention] [mention]Rtj65[/mention]; She was fun!
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